Dimethylamine → HCID 54412888, compound

HRID 377770Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16](OC)(=O)[CH2:17][SH:18].[CH2:22]=O.CNC.CN([CH:30]=[O:31])C>>[C:1]([C:5]1[C:6]([OH:15])=[C:7]([CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)[CH2:22][CH2:16][C:17]([O:31][CH3:30])=[S:18])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 5

HCID 674Dimethylamine

HCID 712Formaldehyde

HCID 6228Dimethylformamide

HCID 73112,4-Di-tert-butylphenol

HCID 16907Methyl Thioglycolate

Product 1

HCID 54412888HCID 54412888, compound

Procedure

50.96 g (0.247 mol) of 2,4-di-t-butylphenol, 28.84 g (0.272 mol) of methyl thioglycolate, 14.83 g (0.494 mol) of paraformaldehyde and 3.41 g of dimethylamine (33% in ethanol) are refluxed for 18 hours in 50 ml of DMF. The crude product (85.3 g) can, after working-up as described above, be further purified by flash chromatography. m.p. 55.0-55.5° C. Analysis for C18H28SO3 : calc. C, 66.63; H, 8.70; S 9.88%; found C 66.65; H 8.79; S 9.88%

Workup

custombe further purified by flash chromatography

Sources & evidence

ORD record: ord-984f85017d274bbbae996576d2f7e856
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028131

Reaction notes

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